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  Unravelling the structure of glycosyl cations via cold-ion infrared spectroscopy

Mucha, E., Marianski, M., Xu, F.-F., Thomas, D. A., Meijer, G., von Helden, G., et al. (2018). Unravelling the structure of glycosyl cations via cold-ion infrared spectroscopy. Nature Communications, 9: 4174. doi:10.1038/s41467-018-06764-3.

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Mucha, Eike, Author
Marianski, Mateusz, Author
Xu, Fei-Fei1, Author              
Thomas, Daniel A., Author
Meijer, Gerard, Author
von Helden, Gert, Author
Seeberger, Peter H.2, Author              
Pagel, Kevin, Author
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              
2Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 Abstract: Glycosyl cations are the key intermediates during the glycosylation reaction that covalently links building blocks during the synthetic assembly of carbohydrates. The exact structure of these ions remained elusive due to their transient and short-lived nature. Structural insights into the intermediate would improve our understanding of the reaction mechanism of glycosidic bond formation. Here, we report an in-depth structural analysis of glycosyl cations using a combination of cold-ion infrared spectroscopy and first-principles theory. Participating C2 protective groups form indeed a covalent bond with the anomeric carbon that leads to C1-bridged acetoxonium-type structures. The resulting bicyclic structure strongly distorts the ring, which leads to a unique conformation for each individual monosaccharide. This gain in mechanistic understanding fundamentally impacts glycosynthesis and will allow to tailor building blocks and reaction conditions in the future.

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Language(s): eng - English
 Dates: 2018-10-092018
 Publication Status: Published in print
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Title: Nature Communications
  Abbreviation : Nat. Commun.
Source Genre: Journal
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Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 9 Sequence Number: 4174 Start / End Page: - Identifier: ISSN: 2041-1723